Stretching cloth to targets
A recent feature somewhere in 2.6x offered up called 'sewing springs' 
http://s6.postimg.org/s0xtlxxkx/sew_Spring0.gif

System depends upon edges to act as pull string, here's how.

Setup pinned vertex group to act as final 'pull' position and anchor. Have it be attached to cloth via extruded 'edges only'.


Followed by a group of edges to bridge distance by pulling.

Enable sewing springs and attach group. 


Add collision detection, bake, rinse and repeat.